Chemical Component Summary

Name2-(ACETYLOXY)BENZOIC ACID
SynonymsACETYLSALICYLIC ACID; ASPIRIN
Identifiers2-acetyloxybenzoic acid
FormulaC9 H8 O4
Molecular Weight180.157
TypeNON-POLYMER
Isomeric SMILESCC(=O)Oc1ccccc1C(=O)O
InChIInChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChIKeyBSYNRYMUTXBXSQ-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count21
Chiral Atom Count0
Bond Count21
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00945 
NameAcetylsalicylic acid
Groups
  • approved
  • vet_approved
DescriptionAlso known as _Aspirin_, acetylsalicylic acid (ASA) is a commonly used drug for the treatment of pain and fever due to various causes. Acetylsalicylic acid has both anti-inflammatory and antipyretic effects. This drug also inhibits platelet aggregation and is used in the prevention of blood clots stroke, and myocardial infarction (MI) [FDA label]. Interestingly, the results of various studies have demonstrated that long-term use of acetylsalicylic acid may decrease the risk of various cancers, including colorectal, esophageal, breast, lung, prostate, liver and skin cancer [A177325]. Aspirin is classified as a _non-selective cyclooxygenase (COX) inhibitor_ [A32682, A177268] and is available in many doses and forms, including chewable tablets, suppositories, extended release formulations, and others [L5968]. Acetylsalicylic acid is a very common cause of accidental poisoning in young children. It should be kept out of reach from young children, toddlers, and infants [FDA label].
Synonyms
  • ácido acetilsalicílico
  • Aspirin
  • Lysine acetylsalicylate
  • 2-Acetoxybenzoic acid
  • O-acetylsalicylic acid
Brand Names
  • Pain Aid ESF
  • Health Mart Migraine Relief
  • Care One migraine relief
  • Enteric Safety Coated Aspirin
  • HyVee Health Effervescent Cold Relief
Indication**Pain, fever, and inflammation** Acetylsalicylic acid (ASA), in the regular tablet form (immediate-release), is indicated to relieve pain, fever, and inflammation associated with many conditions, including the flu, the common cold, neck and back pain, dysmenorrhea, headache, tooth pain, sprains, fractures, myositis, neuralgia, synovitis, arthritis, bursitis, burns, and various injuries. It is also used for symptomatic pain relief after surgical and dental procedures [FDA label]. The _extra strength_ formulation of acetylsalicylic acid is also indicated for the management migraine pain with photophobia (sensitivity to light) and phonophobia (sensitivity to sound)[FDA label]. **Other indications** ASA is also indicated for various other purposes, due to its ability to inhibit platelet aggregation. These include: Reducing the risk of cardiovascular death in suspected cases of myocardial infarction (MI) [FDA label]. Reducing the risk of a first non-fatal myocardial infarction in patients, and for reducing the risk of morbidity and mortality in cases of unstable angina and in those who have had a prior myocardial infarction [FDA label]. For reducing the risk of transient ischemic attacks (TIA) and to prevent atherothrombotic cerebral infarction (in conjunction with other treatments) [FDA label]. For the prevention of thromboembolism after hip replacement surgery [FDA label]. For decreasing platelet to platelet adhesion following carotid endarterectomy, aiding in the prevention of transient ischemic attacks (TIA) [FDA label]. Used for patients undergoing hemodialysis with a silicone rubber arteriovenous cannula inserted to prevent thrombosis at the insertion site [FDA Label]. **Important note regarding use of the extended-release formulation [F4405]** In the setting of acute myocardial infarction, or before percutaneous interventions, the extended-release form of acetylsalicylic acid should not be used. Use immediate-release formulations in scenarios requiring rapid onset of action [Label, F4405]. The extended-release form is taken to decrease the incidence of mortality and myocardial infarction (MI) for individuals diagnosed with chronic coronary artery disease (CAD), including patients with previous myocardial infarction (MI) or unstable angina or with chronic stable angina. Additionally, the extended-release form is used to decrease the risk of death and recurrent episodes of stroke in patients with a history of stroke or TIA [F4405].
Categories
  • Acids, Carbocyclic
  • Agents causing angioedema
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Alimentary Tract and Metabolism
ATC-Code
  • B01AC06
  • C07FX04
  • C10BX04
  • M01BA03
  • N02BA71
CAS number50-78-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Aldo-keto reductase family 1 member C1MDSKYQCVKLNDGHFMPVLGFGTYAPAEVPKSKALEATKLAIEAGFRHID...unknowninhibitor
5'-AMP-activated protein kinaseMRRLSSWRKMATAEKQKHDGRVKIGHYILGDTLGVGTFGKVKVGKHELTG...unknownactivator
Endothelin-1 receptorMETLCLRASFWLALVGCVISDNPERYSTNLSNHVDDFTTFRGTELSFLVT...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL25
PubChem 2244
ChEMBL CHEMBL25
ChEBI CHEBI:15365
CCDC/CSD ACSALA21, ACSALA23, ACSALA14, TAZRAO01, DIFQAK, ACSALA20, DIPJAQ, VUGMIT, ACSALA26, ACSALA15, ARIFOX, KEWNOQ, ACSALA17, ACSALA25, ACSALA01, ACSALA19, SIBYUA, ACSALA27, TAZRAO, HUNJEH, ACSALA28, SIBYUA01, ACSALA02, ACSALA08, ACSALA07, ACSALA05, ACSALA03, ACSALA04, ACSALA06, ACSALA11, ACSALA09, SIBYUA02, ACSALA29, GARYEH, HAPCOU
COD 4100978, 1515581, 1515582, 1516479, 1516480, 1516481, 2104857, 7050897, 7050898, 7050899, 7050901, 7050900, 7050902, 7050903